The present invention relates to a process for production of optically active oxazolidinone derivatives. More particularly, the present invention relates to production of an optically active (S)-(+)-3-alkyl-5-acyloxymethyloxazolidin-2-one having the formula [(S)-II]: ##STR1## wherein X is a lower alkyl group and Y is a substituted or unsubstituted alkyl group, an alkenyl group, or a substituted or unsubstituted aromatic hydrocarbon group, and an optically active (S)-(+)-3-alkyl-5-hydroxymethyloxazolidin-2-one having the formula [(S)-I]: ##STR2## wherein X is as described above, by utilizing the action of a microorganism or an enzyme derived from the microorganism, i.e. the microorganism and enzyme having a stereoselective esterase activity.
The compounds [(S)-II] and [(S)-I] are important intermediates for preparing optically active .beta.-adrenergic blocking agents (hereinafter referred to as ".beta.-blockers").
As processes for preparing optically active .beta.-blockers, there hitherto have been known the following methods:
(1) A method in which a racemate of .beta.-blocker is optically resolved, as disclosed in Japanese Unexamined Patent Publication No. 149233/1980 and U.S. Pat. No. 3,655,663.
(2) A method in which an optically active .beta.-blocker is prepared from an optically active 3-alkylamino-1,2-propanediol obtained by optical resolution of the racemate thereof, as disclosed in Japanese Unexamined Patent Publication No. 118,711/1976.
(3) A method in which an optically active .beta.-blocker is prepared from D-mannitol via D-glycerol acetonide, as disclosed in Journal of Organic Chemistry, 41 (b 19), 3121 to 3124 (1976); Chemical and Pharmaceutical Bulletin, 29 (12), 3593 to 3600 (1981).
However, the method (1) is disadvantageous from the economical point of view because the final product of the racemate is optically resolved. The method (2) cannot easily provide an optically active 3-alkylamino-1,2-propanediol in high yield and high purity by using an optical resolution, because the 3-alkylamino-1,2-propanediol is hygroscopic and poor in crystallization. And the method (3) requires a large amount of lead tetraacetate for preparing D-glycerol acetonide from D-mannitol, and accordingly is not suitable for the industrial production. Thus, these processes include economical or practical problems, and there has not been industrially advantageous process for the production of optically active .beta.-blockers.
On the other hand, the following reaction pathway is known as a rational synthetic pathway for preparing optically active .beta.-blockers, as disclosed in Yoshisuke Tsuda et al: Chemical and Pharmaceutical Bulletin, 29 (12), 3593 to 3600 (1981); Canadian Pat. No. 965,787. ##STR3## wherein X is as described above, Ar is an aryl derivative.
It is an object of the present invention to provide novel and simple processes for producing the compound [(S)-I]. Another object of the present invention is to provide novel and simple processes for producing the compound [(S)-II] which is a useful intermediate for producing the compound [(S)-I].